2-isocyanatoethyl methacrylate

Developments in aliphatic isocyanates include the synthesis of polymeric aliphatic isocyanates and masked or blocked diisocyanates for appflcafions in which volatility or reactivity ate of concern. Polymeric aliphatic isocyanates ate made by copolymerizing methacrylic acid derivatives, such as 2-isocyanatoethyl methacrylate, and styrene [100-42-5] (100). Blocked isocyanates ate prepared via the reaction of the isocyanate with an active hydrogen compound, such as S-caprolactam, phenol [108-95-2] or acetone oxime. 

Shown ate glycidyl methacrylate to introduce epoxide fiinctionahty, acetoacetoxyethyl methacrylate to introduce active methylene groups, dimethylaminoethyl methacrylate to introduce amine fiinctionahty, phosphoethyl methacrylate for strong acid fiinctionahty, and isocyanatoethyl methacrylate to introduce isocyanate fiinctionahty, which may then react with a wide variety of nucleophiles. 

Polyurethane-acrylic coatings with interpenetrating polymer networks (IPNs) were synthesized from a two-component polyurethane (PU) and an unsaturated urethane-modified acrylic copolymer. The two-component PU was prepared from hydroxyethylacrylate-butylmethacrylate copolymer with or without reacting with c-caprolactonc and cured with an aliphatic polyisocyanate. The unsaturated acrylic copolymer was made from the same hydroxy-functional acrylic copolymer modified with isocyanatoethyl methacrylate. IPNs were prepared simultaneously from the two-polymer systems at various ratios. The IPNs were characterized by their mechanical properties and glass transition temperatures. 

Raw Materials. The raw materials used in this study are shown in Table l. The isocyanatoethyl methacrylate (lEM) was distilled before use. The solvent was dried by a 4A molecular sieve overnight before use. The other materials were used as received. 

Isocyanatoethyl methacrylate Dow Chemical Co. t-Butyl perbenzoate Lucidol Corp. 

The synthesis of the module is provided in Scheme 10.5 (Kushner et al. 2007). Double alkylation of ethyl acetoacetate followed by guanidine condensation afforded alkenyl-pyrimidone intermediate 24 (Kushner et al. 2007). Isocyanate 25 was coupled to pyrimidone 24 to yield 26. Upon dimerization in DCM, RCM effectively cyclized the two UPy units (Mohr et al. 1997 Week et al. 1999). A one-pot reduction and deprotection through hydrogenation using Pearlman s catalyst gave diol module 27. Finally, capping 27 with 2-isocyanatoethyl methacrylate at both ends provided the UPy sacrificial cross-linker 28, which was thoroughly characterized by H- and C-NMR, Fourier transform IR (FTIR), and mass spectrometry. 

Hydroxybutyl lignin, as well as lignin and lignin derivative-like model compounds, were chemically modified by reaction with isocyanatoethyl methacrylate (IEM). 

Materials. Difunctional Reagents Isocyanatoethyl methacrylate (IEM) was supplied by Dow Chemical Co. as an experimental reagent. Meta TMI is available from Cyan amid, Inc. 

The mouse sensory irritation potentials of HDI, toluene-2,4-diisocyanate (TDI), isocyanatoethyl methacrylate (lEM), and isocyanatoethyl propionate (lEP) were determined in another study. Male Swiss albino CD-I mice were exposed for a 2-minute control period with room air, 3 minutes of exposure to one of 4 isocyanate vapors, then 2 minutes of recovery with room air. The range of concentrations tested were 0-0.82 ppm for HDI, 0-3.44 ppm for TDI, 0-2.51 ppm for lEM, and 0-1.95 ppm for lEP. The concentration that produced RDjo was determined. HDI was determined to be approximately 3 times... 

Graham, R. K. Preparation of graft copolymers by the reaction of primary amine-terminated polystyrene with copolymers containing /3-isocyanatoethyl methacrylate. J. Polymer Sci. 24, 367 (1957). 

ISOCYANATOETHYL METHACRYLATE see IKG700 P-ISOCYANATOETHYL METHACRYLATE see IKG700 ISO-CYANATOMETHANE see MKX250 1-ISOCYANATO-2-METHYLBENZENE see IKG725 l-(l-ISOCYANATO-l-METHYLETHYL)-3-(l-METHYLETHENYL)BENZENE see IKG800... 

Dibutyltin dilaurate (DBTDL) (M T Chem. Co.), 1,4-diaza [2,2,2.]. octane (Air Products), isocyanatoethyl methacrylate (IEM) and carbamoyl chloride of IEM (Dow Chem. Co.) and hexamethylene diisocyanate were used as supplied. Phenyl isocyanate, p-tolyl isocyanate, p-chlorophenyl Isocyanate (all Aldrich Chem. Co.), 2-ethoxyethyl acetate (Eastman Kodak Co.) and n-butanol (Mallinkrodt) were purified by distillation before use. 

Isocyanatoethyl methacrylate/n-butanol (1 1) DBTDL solvent n-butyl acetate, 25°C. 

Multiple methyl substituents in TMDI inhibit intermolecular associations of the urethane segments derived from these building blocks and hence promote flexibility in the resulting PURs. An interesting heterodifunctional isocyanate is Dow s isocyanatoethyl methacrylate (IEM)... 

This method has been applied to a monomer synthesis (2.20).61 The quaternary ammonium salt is used as a phase transfer catalyst. The potassium iodide converts the starting chloride to a more reactive iodide in situ. The alcohol traps the intermediate isocyanate before it can react with the small amount of water that has to be present. If no methanol is present, the corresponding urea is formed in up to 87% yield. If only 0.3 equivalent of water is used, the product is the iso-cyanurate, the cyclic trimer of the isocyanate. Where n = 1, the isocyanatoethyl methacrylate is a useful monomer now made with phosgene (2.21).62 Dow has patented a route from ethanolamine plus a dialkyl carbonate, followed transesterification to a methacrylate carbamate, which is py-rolyzed to the isocyanate (2.22) in 50% yield.63... 

The Dow Chemical Co. has recently been offering isocyanatoethyl methacrylate (IBM) ... 

The postintroduction of hydrophobes could offer an effective alternative to the mutual solubility problems (Chapter 20) encountered in chain-growth copolymerizations. The introduction of difunctional monomers that contain both unsaturation and isocyanate units (e.g., isocyanatoethyl methacrylate or m-isopropenyl a,a-dimethylbenzylisocyanate) with lower cost non-iso-cyanate-containing monomers (45) provides two routes for postmodification. One route could be the copolymerization with methyl acrylate, followed by the reaction of the isocyanate function with an ethoxylated surfactant, then hydrolysis of the methyl acrylate units. 

New monomers have been introduced which combine both unsaturation in with isocyanate groups. For example, 2-isocyanatoethyl methacrylate (Dow) has been reported to give a mixture of trimer and polymers using titanium complexes (Tyzor DC from DuPont) which still has unsaturation [2bj. The resulting polymer can possibly be crosslinked via the unsaturated part of the molecule. 

Methacrylate esters have been prepared by the reaction of methacrylic acid with epoxies such as the diglycidyl ethers of bisphenol A (XXXVII) [37]. Methacrylate esters suitable for anaerobic adhesives have also been prepared by the reaction of glycidyl methacrylate (XXXVIII) with a hydroxyl-terminated polyester [38]. The reaction of isocyanatoethyl methacrylate (XXXIX) with polyols resulted in monomers that could be formulated into anaerobic adhesives and sealants [39]. 

Isocyanatoethane. See Ethyl isocyanate Isocyanatoethyl methacrylate. See 2-Isocyanatoethyl methacrylate... 

Synonyms I EM Isocyanatoethyl methacrylate P-lsocyanatoethyl methacrylate Methacrylic acid, 2-isocyanatoethyl ester Methacryloyloxyethyl isocyanate 2-Propenoic acid, 2-methyl, 2-isocyanatoethyl ester... 

Methacryloyl ethyl betaine/methacrylates copolymer. See Methacryloyl ethyl betaine/acrylates copolymer 2-(Methacryloyloxy) ethyl acetoacetate. See 2-(Acetoacetoxy) ethyl methacrylate Methacryloyloxyethyl isocyanate. See 2-Isocyanatoethyl methacrylate (3-Methacryloyloxypropylj trimethoxysilane. 

Diethylaminoethyl acrylate Diethylaminoethyl methacrylate coatings, automotive Dimethylaminoethyl methacrylate 2-Isocyanatoethyl methacrylate coatings, automotive protective Chromium coatings, barrier... 

Isocyanatoethyl Methacrylate A Latent Crosslinker for Coating Adhesive Resins... 

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